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Cuckold and escorting #1
17/09/2024
This will probably take 3 stories to tell of the adventure Lynn and i just had in Philadelphia. Not only does she cuckold me she also is a high priced escort occasionally and this past weekend was probably the best we've ever had.

We're both in our late forties, hit the gym at least five times a week. Lynn is 5'3", 105lbs, 34c breasts with a pierced clit and nipple rings she loves to show off. We both have tight abs and butts, toned but not bulky.

Three weeks prior to traveling to a different city Lynn advertises her services on an escort website for Thursday evening, Friday and Saturday. We also take a couples services ad out for a BDSM scene to be watched by a couple or a single guy on Sunday.

Lynn locks my cock up in my Kali cage the day we take out the ads. I can only lick, finger or use a toy on her up until the Sunday prior to us leaving. She wants to be tight and horny. She also gets a STD test to be sure she's safe and only plays with guys that supply one of their own. She is a size queen as my 6.5"cock is okay but the bigger the better. She screens all applicants and sets her dates.

We left for Philly this past Thursday, me in my cock cage, her in a mini skirt, white camisole and jacket. No bra or panties. Once we were cleared by the gate agent, Lynn handed me her jacket and said I sure hope guys like seeing my pierced nipples b/c this AC air has them pointing straight out. We always get an aisle and middle seat for Lynn so my right hand can tease her on the plane. The young man next to her enjoyed watching me finger her.

We stayed downtown at a Five star hotel that has a gym, bar and restaurant ( Lynn likes to tease room service boys by answering the door nude). We arrived early morning and went sight seeing. We returned shortly after lunch so we could use the gym. As usual Lynn wore a solid colored sports bra and some booty shorts. The two guys in the gym really enjoyed watching her use the machines as did I.

By 3:30 our adjourning rooms were ready and we went up to get ready for her first "date". While Lynn was showering I order a fruit trey for her room and waited in her room for room service. When the knock came Lynn insisted on answering it buck naked and gave the young man a nice thank you kiss.

We headed to the bar at 4:45 as her date was to arrive at 5. Lynn was dressed in a very low cut and short cocktail dress, no bra and a g string panty. We sat at different sides of the bar waiting for her date. He arrived right on time, dark hair, 6'2', toned and a great smile when he saw Lynn. They sat at the bar and chatted, then moved to a table against the wall. I watched as they talked and laughed. They seemed to be enjoying each others company as their hands were under the table. I'm sure his grin came from feeling how soaked her g string was. They got up to head to the room when I heard her say I need to go to the restroom. On her way out she passed by me and dropped her g string on the bar and said "I'm having a good time tonight".

I gave them ten minutes to have a head start and headed up to my adjourning room. The doors were cracked so i could not only listen but after he left enter without her getting up. I could hear Lynn slurping his massive cock, hear him eating her sexy pierced pussy and her begging for his cock. Then I listened as he pounded her pussy, getting Lynn to scream in pleasure. He asked where can I cum and she asked can you go again? He said yes so she said fill my pussy and shortly after I heard him groan in ectasy. Lynn I'm sure cleaned his cock with her mouth as shortly after I heard him saying how good her mouth felt. The slurping stopped for a second and then Lynn said please cum on my breasts as I want them glowing with your cum while I have dinner with my boyfriend. That comment was all it took for him to unload all over her sexy pierced breasts.

She said thanks for that my boyfriend will love the view. His hour was up as he dressed, kissed her goodbye and said I hope I can see you again. Once the door closed I entered to see her laying on the bed, her pussy red and wet and her breasts still drenched in cum. I went down and cleaned her pussy like a good cuckold, gave her two big orgasms and a very wet kiss.

Lynn slipped on a short, plunging dress being careful not to remove the cum for our dinner date. She put nipple clamps around her neck for a neckless and off we went back down for dinner. Obviously she was in a different outfit with a different guy so I'm sure folks were talking. Dinner was an appetizer, salad and we split an entree as her second date was at nine and she needed to be rested and cleaned up.

My cock was straining inside the Kali cage as she rubbed it in my pants on the elevator. Lynn said Sunday will be here soon enough and I need you ready to ravish me, beat me and fuck me harder for the couple that's signed up to watch our BDSM scene.

Once in the room, Lynn showered, reapplied her make up and we headed to the bar for her second evenings "date". The first guy was white so I was surprised that her second date was a large black guy. He also was attractive, dressed professionally and kissed her hand when he met her. That was a good start. They headed straight to the room and I sat and nursed two scotches as I assumed she'd be in no rush to enjoy her new toy. After 45 minutes I went up to listen and when I was in the hall the sound of love making was very prevelant. Someone was getting pounded very hard, screaming and moaning loudly and asking for it to be harder. What was supposed to be an hour and a half meeting turned into three hours of Lynn taking his cock in all her holes and losing track of how many times she came. He left about midnight as Lynn lay on the bed completely exhausted but very satisfied. Her breasts had hickeys, her pussy and ass were swollen, her body was covered in cum and sweat and she looked so DAMN sexy I had to eat her as she mounted my face.

She said she was glad we can sleep in on Friday as her next date is right after lunch.


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